Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate

Base Information

• Chemical Name: Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate
• CAS No.: 175854-39-4
• Molecular Formula: C23H44 N4 O6
• Molecular Weight: 472.626
• Hs Code.: 29339900
• European Community (EC) Number: 635-789-6
• DSSTox Substance ID: DTXSID60447053
• Nikkaji Number: J1.079.330K
• Wikidata: Q72509870
• Mol file: 175854-39-4.mol

Synonyms:175854-39-4;Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate;1,4,7-Tri-Boc-1,4,7,10-tetraazacyclododecane;N,N',N''-tris-Boc-cyclen;1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane;tritert-butyl 1,4,7,10-tetrazacyclododecane-1,4,7-tricarboxylate;1,4,7-tri-Boc-1,4,7,10-tetraaza-cyclododecane;C23H44N4O6;N,N',N''-Tri-Boc-cyclen;SCHEMBL2220355;AMY7627;DTXSID60447053;MFCD09953471;AKOS015911763;CS-W004649;DS-4003;1,4,7,10-Tetraazacyclododecane-1,4,7-tricarboxylic acid, 1,4,7-tris(1,1-dimethylethyl) ester;A3904;FT-0721142;J-011140;1,4,7-Tri-Boc-1,4,7,10-tetraazacyclododecane, 98%;1,4,7-Tris(tert-butoxycarbonyl)-1,4,7,10-tetraazacyclododecane;1,4,7-tris-(t-butyl-oxycarbonyl)-1,4,7,10-tetraazacyclododecane;Tri-tert-Butyl1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate;1,4,7-tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate;1,4,7,10-Tetraazacyclododecane-1,4,7-tricarboxylicacid,1,4,7-tris(1,1-dimethylethyl)ester

Chemical Property of Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate

Chemical Property:

• Vapor Pressure: 9E-12mmHg at 25°C
• Melting Point: 72-73℃
• Boiling Point: 541.1°Cat760mmHg
• PKA: 9.52±0.20(Predicted)
• Flash Point: 281°C
• PSA: 100.65000
• Density: 1.11g/cm³
• LogP: 3.44340
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 472.32608514
• Heavy Atom Count: 33
• Complexity: 621

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,4,7-tri-Boc-1,4,7,10-tetraaza-cyclododecane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCNCCN(CCN(CC1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
• Uses: Building block used to attach the Cyclen azacrown to a molecular scaffold, building block for a trifold cyclen Zn complex as phosphate dianion receptor in aqueous solution

Technology Process of Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate

There total 6 articles about Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.3%

di-tert-butyl dicarbonate (24424-99-5) + 1,4,7,10-tetraazacyclododecan (294-90-6) → 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane (175854-39-4) + 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane (913528-02-6)

Guidance literature:

In chloroform; at 20 ℃;

DOI:10.1016/j.tetlet.2006.07.135

Reference yield: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + 1,4,7,10-tetraazacyclododecan (294-90-6) → 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane (175854-39-4)

Guidance literature:

With triethylamine; In chloroform;

DOI:10.1039/c2jm32726k

Reference yield: 90.0%

1-benzyloxycarbonyl-4,7,10-tris-tert-butoxycarbonyl-1,4,7,10-tetraazacyclododecane (188903-14-2) → 1,4,7-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane (175854-39-4)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1021/ja9640408

upstream raw materials:

di-tert-butyl dicarbonate

1,4,7,10-tetraazacyclododecan

1-benzyloxycarbonyl-4,7,10-tris-tert-butoxycarbonyl-1,4,7,10-tetraazacyclododecane

cyclen tetratosylate

Downstream raw materials:

1-benzyloxycarbonyl-4,7,10-tris-tert-butoxycarbonyl-1,4,7,10-tetraazacyclododecane

1-bromomethyl-4-(4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane-1-ylmethyl)benzene

1,3-bis(1,4,7-tris[tert-butyloxycarbonyl]-1,4,7,10-tetraaza-cyclododecan-1-yl)-4,6-dinitro-benzene

10-(3-benzyloxycarbonylamino-propyl)-1,4,7,10-tetraaza-cyclododecane-1,4,7-tricarboxylic acid tri-tert-butyl ester

Refernces

• 1、 da Silva, Sara R.,Paiva, Stacey-Lynn,Bancerz, Matthew,Geletu, Mulu,Lewis, Andrew M.,Chen, Jijun,Cai, Yafei,Lukkarila, Julie L.,Li, Honglin,Gunning, Patrick T.. "A selective inhibitor of the UFM1-activating enzyme, UBA5". . p. 4542 - 4547. Retrieved 2016.
• 2、 Fang, Yu-Guo,Zhang, Ji,Chen, Shan-Yong,Jiang, Ning,Lin, Hong-Hui,Zhang, Yu,Yu, Xiao-Qi. "Chiral multinuclear macrocyclic polyamine complexes: Synthesis, characterization and their interaction with plasmid DNA". . p. 696 - 701. Retrieved 2007.
• 3、 Anju,Chaturvedi, Shubhra,Chaudhary, Vishakha,Pant, Pradeep,Jha, Preeti,Kumaran, Senthil S.,Hussain, Firasat,Kumar Mishra, Anil. "5-HT1A targeting PARCEST agent DO3AM-MPP with potential for receptor imaging: Synthesis, physico-chemical and MR studies". . . Retrieved 2021.
• 4、 Venkatachalam,Barreto, Jose,Kreher, Ute,Reutens, David C.,Spiccia, Leone. "Synthesis, characterization and coordination chemistry of dibenzofuran derivatives of 1,4,7,10-tetraazacyclododecane". . p. 2896 - 2904. Retrieved 2010.
• 5、 Hwang, Sangyeul,Cha, Wansik,Meyerhoff, Mark E.. "Polymethacrylates with a covalently linked CuII-cyclen complex for the in situ generation of nitric oxide from nitrosothiols in blood". . p. 2745 - 2748. Retrieved 2006.
• 6、 Dolan, Ciarán,Drouet, Fleur,Ware, David C.,Brothers, Penelope J.,Jin, Jianyong,Brimble, Margaret A.,Williams, David E.. "A new high-capacity metal ion-complexing gel containing cyclen ligands". . p. 23645 - 23652. Retrieved 2016.
• 7、 Liu, Kun,Meyerhoff, Mark E.. "Preparation and characterization of an improved Cu2+-cyclen polyurethane material that catalyzes generation of nitric oxide from S-nitrosothiols". . p. 18784 - 18787. Retrieved 2012.
• 8、 -. "DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX". Paragraph 0060-0061. . Retrieved 2021/03/19.